Explore Homes for Sale in Winter Garden, FL
Map Search for Winter Garden, FL Homes for Sale

Discover Your Dream Home: Explore Winter Garden, FL Homes For Sale with The Nest Group

  Advanced Search   Market Reports   Home Value   Connect

Winter Garden, FL, offers a vibrant real estate market with diverse homes for sale, perfect for every lifestyle. From charming historic bungalows in the downtown area to modern family residences in master-planned communities like Hamlin and Horizon West, prospective buyers will discover unparalleled opportunities. The Nest Group specializes in helping you navigate the unique offerings of Winter Garden, ensuring you find a property that perfectly matches your dreams. Explore the latest listings, experience the welcoming community spirit, and imagine life amidst beautiful natural surroundings and convenient access to Central Florida's best attractions. Your ideal Winter Garden home awaits.

Search Winter Garden, FL by Lifestyle
Search Winter Garden, FL by Price
Search Winter Garden, FL by Bedrooms
Search Winter Garden, FL by Bathrooms
Winter Garden, FL Communities

Exploring Winter Garden's Diverse Real Estate Landscape

A Spectrum of Homes for Sale in Winter Garden, FL

Winter Garden, Florida, consistently ranks as one of Central Florida's most sought-after locations for new residents. Consequently, the inventory of homes for sale here is remarkably varied, appealing to a wide array of preferences and budgets. Whether you're seeking a quaint starter home or an expansive luxury estate, the Winter Garden real estate market presents a compelling selection.

Historic Charm Meets Modern Living: Downtown Winter Garden Homes

For those enchanted by character and community, downtown Winter Garden homes offer a unique appeal. Nestled around the iconic Plant Street, you'll find beautifully preserved and meticulously renovated bungalows and historic properties for sale. These residences provide direct access to the vibrant Plant Street Market, local eateries, boutiques, and the scenic West Orange Trail, embodying a truly walkable lifestyle.

New Construction Homes in Horizon West & Beyond

On the flip side, the sprawling Horizon West area, a significant part of Winter Garden, is a hub for new construction homes. Neighborhoods like Hamlin, Lakeside Village, Summerport, Independence, and Storey Grove feature an abundance of newly built homes for sale, often within master-planned communities. These areas are renowned for their state-of-the-art amenities, top-rated schools, and family-friendly environments, offering modern designs and energy-efficient features perfect for contemporary living.

Lifestyle & Community: What Makes Winter Garden Homes So Desirable?

Embrace the Winter Garden Lifestyle

Beyond the impressive selection of homes for sale, Winter Garden boasts a lifestyle that truly sets it apart. Residents enjoy a harmonious blend of small-town charm and big-city conveniences. Weekends can be spent cycling the West Orange Trail, exploring the Farmers Market, or enjoying live music and events on Plant Street. The close-knit community actively participates in local festivals and gatherings, fostering a genuine sense of belonging.

Family-Friendly Amenities and Top-Rated Schools

Families consistently choose Winter Garden for its exceptional quality of life. The community is home to numerous parks, recreational facilities, and highly-rated public and private schools, making it an ideal place to raise children. When considering homes for sale, the proximity to these essential family amenities often plays a crucial role in the decision-making process for many prospective buyers.

Finding Your Perfect Match: Types of Homes for Sale in Winter Garden

Single-Family Homes: Space and Serenity

The majority of homes for sale in Winter Garden are single-family residences, offering diverse architectural styles and lot sizes. From spacious suburban homes with private yards to elegant properties in gated communities like Oakland Park, there's a single-family home to suit every family's needs, providing ample space for growth and personalization.

Townhomes & Villas: Convenient Winter Garden Living

For those seeking a lower-maintenance lifestyle without compromising on location or amenities, Winter Garden also offers an excellent selection of townhomes and villas for sale. These properties are often found in communities with shared amenities like pools and clubhouses, presenting an attractive option for first-time buyers, downsizers, or those seeking a convenient lock-and-leave lifestyle near all local conveniences.

Luxury & Waterfront Homes for Sale in Winter Garden

Winter Garden's real estate market also caters to the luxury segment, featuring exquisite estates and waterfront homes for sale. Properties overlooking Lake Apopka or situated in exclusive enclaves offer premium finishes, expansive living spaces, and often private docks or stunning natural views. These luxury homes represent the pinnacle of Winter Garden living, combining elegance with a coveted Central Florida address.

Navigating the Winter Garden Real Estate Market

The Nest Group: Your Local Winter Garden Real Estate Experts

Successfully navigating the dynamic Winter Garden real estate market requires local expertise and insight. As your dedicated real estate partners, The Nest Group brings unparalleled knowledge of Winter Garden's neighborhoods, market trends, and hidden gems. We are committed to helping you discover the ideal homes for sale that align with your vision and lifestyle in this beautiful Central Florida community.

Newest Homes for Sale in Winter Garden, FL

$409,990
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Rare opportunity to own one of the largest townhome lots in the highly sought-after Waterleigh community in Horizon West. This beautifully maintained 3-bedroom, 2.5-bath IBIS model townhome, built in 2020, offers 1,568 sq ft of thoughtfully designed living space and sits on an oversized lot of approximately 4,100 sq ft — nearly double the lot size of many newer townhomes in the community. One of the most exceptional features of this property is the extended driveway with space for up to 6 vehicles, in addition to the 1-car garage — a rare and highly desirable feature among townhomes in Waterleigh, perfect for families and guests. Inside, the home features a bright open-concept layout with a modern kitchen, spacious living and dining areas, and abundant natural light throughout. Upstairs, you’ll find well-sized bedrooms, including a comfortable primary suite with walk-in closet and private bath. Step outside and enjoy the added outdoor space that truly sets this property apart — ideal for relaxing, entertaining, or simply enjoying extra privacy. Waterleigh offers resort-style amenities including multiple pools, clubhouse, fitness areas, parks, walking trails, and top-rated schools nearby, all within one of the fastest-growing areas of Horizon West.

16209 Admirals Cove Lane, Winter Garden
$347,500
3 Beds ⋅ 3 Baths ⋅ Tucker Oaks Bldg 5 SubDv. ⋅ 34787 Zip Code
Welcome to this spacious 3 bedroom 2.5 bath home situated on a quiet cul-de-sac with no rear neighbors and low HOA in the highly desirable Winter Garden area! This well maintained property features an open and functional floor plan with generous living spaces and abundant natural light, ideal for both everyday living and entertaining. The kitchen offers ample cabinet and counter space, flowing seamlessly into the main living areas. The primary suite provides a comfortable retreat with a private bath, while two additional bedrooms offer flexibility for family, guests, or a home office. Enjoy a private screened patio perfect for relaxing or hosting gatherings. Prime location, just minutes from everything Winter Garden has to offer! Conveniently located near shopping, dining, and entertainment with easy access to Highway 50 and the Florida Turnpike. Don’t miss this opportunity, schedule your private showing today!

15353 Oak Apple Court, Winter Garden
$714,999
3 Beds ⋅ 2 Baths ⋅ Woodbridge On Green SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring spacious living areas, high ceilings, and thoughtfully designed spaces that make everyday living effortless. The kitchen offers generous counter space, ample cabinetry, and a functional layout perfect for cooking, entertaining, or gathering with family. The primary suite provides a peaceful retreat with a well-appointed bathroom and plenty of closet space. Additional bedrooms are comfortably sized and versatile—ideal for guests, a home office, or a growing household. Outside, enjoy a very large private backyard on the pond, with room to relax, garden, or entertain. New concrete tile roof was installed in 2023. Woodbridge on the Green is known for its mature landscaping (fully HOA maintained), quiet streets, and welcoming atmosphere; the HOA also covers house painting on a rotating schedule, helping to ensure an immaculate community aesthetic. Located just minutes from Windermere, top-rated schools, major highways, and the charming Historic Downtown Winter Garden, this home offers unmatched convenience with shopping, dining, and entertainment right at your fingertips. This is a wonderful opportunity to own a home in one of Winter Garden’s most desirable neighborhoods—move-in ready and full of potential.

14050 Fairway Willow Lane, Winter Garden
$560,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3a SubDv. ⋅ 34787 Zip Code
Waterleigh! In this master planned community lies this beautiful two story, with all new exterior paint, three bedroom, two and a half bathroom, with a second floor den/flex space, which is perfect for a home office or kids space.! The spacious kitchen features stainless steel appliances, stone countertops, new backsplash and a large island/breakfast bar. This open plan has a large living room/dining room combo with crown molding and a sliding glass door which opens up to the covered lanai area. The master bedroom is on the first floor and has a new tile floor. The owners bath features a walk in shower, double sinks and stone counter top, as well as a walk in closet and a separate linen closet for convenience and extra storage. The laundry area is located on the first floor. Upstairs, you will find two additional bedrooms, a full bath and flex area. This home features an attached rear 2 car garage entrance with convenient drop zone with lots of cabinets for extra storage and granite counter top. Residents have access to four incredible amenity centers with resort-style pools, offering 2 stunning clubhouses with fitness centers, putt putt golf, beach volleyball, tennis, pickleball, BBQ/picnic areas, playground, & dog park. Even better, LANDSCAPING IS INCLUDED in the HOA, allowing you to spend less time on yard work and more time enjoying the community. This property is conveniently located nearby to shopping, grocery stores, restaurants, and hospitals, alongside being close to Walt Disney World, which makes it a magical place to live! Home available to view no appointment needed come take a look .

16933 Oakboro Street, Winter Garden
$2,250,000
5 Beds ⋅ 5 Baths ⋅ Summerlake Pd Ph 2a & 2b SubDv. ⋅ 34787 Zip Code
Experience of luxury living in this 2021 custom-built contemporary masterpiece by Davila Homes with acess to Lake Hancock-a highly sought after ski lake. Boasting five bedrooms, a dedicated office and a loft, this residence seamlessly blends modern design with the tranquility of lakeside living. Step inside to discover an open, sunlit space connecting the living room, dining area, and chef's kitchen. Expansive windows frame panoramic lake views, creating an inviting atmosphere throughout. The owner's bedroom, complete with a custom walk-in closet, provides comfort and convenience. Beyond the ordinary, this home features a expansive windows, surround sound throughout the home and an oversized laundry room. The floor-to-ceiling stackable sliding doors allow you to step outside to your private paradise with a saltwater pool with a spa and a boat dock. Enjoy a low-maintenance turf yard, ensuring lush greenery year-round. As part of a vibrant community, residents enjoy access to Resident's Club, featuring a state-of-the-art fitness center, business center, resort-style pool with splash pad, playground, tennis and basketball courts. Conveniently located just minutes from the Hamlin Center and 429, this residence offers a perfect blend of serenity and accessibility. Don't miss the chance to call this lakefront haven home.

7701 Summerlake Pointe Boulevard, Winter Garden
$1,300,000
5 Beds ⋅ 4 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
PRICE IMPROVEMENT! Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the interiors are bright and inviting. Recent enhancements include new exterior paint (2026), a tankless water heater (2026), and a added ensuite bathroom (2026) making two primary suites on the second floor. Generous storage is thoughtfully integrated with expansive closet space, while a whole-home water softener and purification system, including an under-sink filter, ensures elevated everyday comfort. At the heart of the home, the gourmet kitchen is both functional and beautifully appointed, featuring dual sinks, a dedicated prep island, and upgraded soft-close cabinetry. The oversized three-car garage provides ample room for vehicles, storage, or recreational needs. Outdoors, the lifestyle truly unfolds. A recently resurfaced covered boat dock—complete with lift, lighting, fan, and sink—offers direct access to one of Florida’s largest spring-fed lakes, part of the Harris Chain and extending to the St. Johns River and Atlantic Ocean. The expansive grounds are enriched by mature, fruit-bearing trees including mango, avocado, star fruit, and citrus, creating a lush, private retreat. Surrounded by natural beauty, the property attracts an impressive array of wildlife. Unforgettable sunrises and sunsets can be enjoyed from multiple vantage points, including the living spaces, patio, dock, and three north-facing bedrooms with water views. This is a home that seamlessly balances elegance and ease—offering a rare opportunity to experience serene waterfront living in one of Winter Garden’s most iconic settings.

243 Zachary Wade Street, Winter Garden
$530,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4a SubDv. ⋅ 34787 Zip Code
NEARLY NEW "BELLAKE" MODEL HOME featuring 3 bedrooms and 2.5 bathrooms, situated on a PREMIUM LOT just a short Walk to the BRAND NEW Phase 4 POOL & GYM, Atwater Bay Elementry School, Waterfront Park and Community Playground! Excellent features include Upgraded Rectangular Tile throughout the first floor! A GOURMET KITCHEN with Shaker Cabinets, GRANITE Countertops, and Stainless Steel Appliances (including a French-door Refrigerator) an oversized ISLAND and a LARGE Walk-In Pantry. Great OPEN CONCEPT FLOOR PLAN: The kitchen opens directly into the dining area, and the family room overlooks a COVERED PATIO—offering the perfect space for RELAXING, Chilling and Grilling! The FLEX SPACE at the front of the home serves perfectly as an Office or Formal Dining Room - or ADD a DOOR and Make Bedroom 4! SUPERIOR STORAGE options abound, including a DROP ZONE area with a Closet and 6 Feet of Cabinetry and Counter Space! PLUS there is a HUGE under the stairs Storage Closet AND a front Hallway Closet! A convenient Powder Room completes the First Floor. Upstairs, you will find a spacious Primary Suite with a Bath featuring DOUBLE SINKS, LARGE Shower, Upgraded Cabinets, Granite Counters, a Linen Closet and a generous 10' x 6' Walk-In Closet. Bedrooms 2 and 3 share a Full bathroom with DOUBLE Sinks! The Laundry Room includes a Front Load Washer and Dryer! This Energy Efficient home SAVES you $$$ on Utility bills. Gutters have been added, and the LONG Driveway provides ample additional Parking Space. The HOA handles all Lawn Maintenance, allowing you to fully ENJOY this PREMIER Lifestyle Community—which boasts 4 RESORT Style Pools, 3 Clubhouses, 3 Fitness Centers, Beach Volleyball, Tennis Courts, Parks, Playgrounds, Special Events, and Vews of the DISNEY Fireworks! Zoned for the NEW Atwater Bay Elementary, Water Spring Middle, and Horizon High School. Close to theme parks, shops, restaurants, and the 429!

13617 Salamander Street, Winter Garden
$179,950
2 Beds ⋅ 2 Baths ⋅ Grove Resort & Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Experience the ultimate Orlando resort lifestyle and investment opportunity at The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations located just minutes from Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. This fully furnished, turnkey condominium offers a spacious open-concept layout with a beautifully designed kitchen, bright great room, oversized windows, and a private balcony with peaceful courtyard view—perfect for enjoying Florida’s sunshine and serene surroundings. The living room also has a sleeper sofa so it comfortably sleeps 6 guests. Designed for both comfort and flexibility, this condo features 2 bedrooms with a split layout for added privacy, spacious living areas, and 2 spa-inspired bathrooms with features such as garden tubs, tiled showers, and dual vanities. Large-screen televisions, modern finishes, and stylish furnishings create a welcoming retreat for owners and guests alike. This is a comfortable place to unwind after a day of fun. The Grove Resort is a world-class, family-friendly destination offering exceptional amenities and a true “escape within an escape.” The highlight is the spectacular Surfari Water Park, featuring a FlowRider® surf simulator, dueling water slides, lazy river, splash park, activity pool, zero-entry pool, and private cabanas with food and beverage service. Guests also enjoy access to multiple resort pools, hot tubs, and a 20-acre activity lake with a private dock ideal for fishing or relaxing by the water. Additional amenities include Longboard Bar & Grill, Valencia Restaurant, Element Bar & Lounge, Alfresco Market, Byte grab-and-go market, Flip Flop’s Family Fun Center, arcade, game room, and on-site dining and entertainment. Relax and recharge at the full-service spa and modern fitness center, or enjoy the convenience of daily shuttle transportation to Disney World, Universal Studios, and SeaWorld. Ownership is truly hassle-free, with professional on-site hotel management handling bookings, guest services, and maintenance, making this an ideal hands-off income-producing investment property or personal vacation retreat. With its unbeatable location, incredible amenities, and strong rental potential, The Grove Resort offers the perfect combination of luxury, lifestyle, and investment value in the heart of Orlando’s world-famous attractions. **CHECK OUT the virtual tour! Its a 3D Matterport, an Immersive digital model of the property. You can choose a room and see 360 degrees, and floor to ceiling, as well as walk through room to room.**

14501 Grove Resort Avenue Unit 1732, Winter Garden
$194,950
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Experience the ultimate Orlando resort lifestyle and investment opportunity at The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations located just minutes from Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. This fully furnished, turnkey condominium offers a spacious open-concept layout with a beautifully designed kitchen, bright great room, oversized windows, and a private balcony with sought after peaceful WATER AND POOL VIEW —perfect for enjoying Florida’s sunshine and serene surroundings. Designed for both comfort and flexibility, this condo features 2 bedrooms with a split layout for added privacy, spacious living areas, and 2 spa-inspired bathrooms with features such as garden tubs, tiled showers, and dual vanities. Large-screen televisions, modern finishes, and stylish furnishings create a welcoming retreat for owners and guests alike. The living room also has a sleeper sofa so it comfortably sleeps 6 guests. This is a comfortable place to unwind after a day of fun. The Grove Resort is a world-class, family-friendly destination offering exceptional amenities and a true “escape within an escape.” The highlight is the spectacular Surfari Water Park, featuring a FlowRider® surf simulator, dueling water slides, lazy river, splash park, activity pool, zero-entry pool, and private cabanas with food and beverage service. Guests also enjoy access to multiple resort pools, hot tubs, and a 20-acre activity lake with a private dock ideal for fishing or relaxing by the water. Additional amenities include Longboard Bar & Grill, Valencia Restaurant, Element Bar & Lounge, Alfresco Market, Byte grab-and-go market, Flip Flop’s Family Fun Center, arcade, game room, and on-site dining and entertainment. Relax and recharge at the full-service spa and modern fitness center, or enjoy the convenience of daily shuttle transportation to Disney World, Universal Studios, and SeaWorld. Ownership is truly hassle-free, with professional on-site hotel management handling bookings, guest services, and maintenance, making this an ideal hands-off income-producing investment property or personal vacation retreat. With its unbeatable location, incredible amenities, and strong rental potential, The Grove Resort offers the perfect combination of luxury, lifestyle, and investment value in the heart of Orlando’s world-famous attractions.

14501 Grove Resort Ave Unit 3621, Winter Garden
$653,118
4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | North Facing Lot | Premium Location | Game Room. New Construction - August Completion! Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath is in place of the flex room, creating a convenient option for guests or work-from-home needs. At the back of the home, the covered extended lanai provides a sunny space for outdoor revitalization. Upstairs, the exceptional primary suite features a dual-sink vanity and walk-in shower, with the laundry room and secondary bedrooms nearby. The spacious game room over the garage includes its own full bath and wet bar, creating an ideal space for casual gatherings. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: game room over garage with full bath and wet bar, first floor bedroom with full bath in place of flex room, covered extended lanai, 8' interior doors throughout. Photos are for representative purposes only. MLS#O6391463

14780 Field Daisy Drive, Winter Garden
$553,690
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully upgraded home located in one of the most desirable areas of Winter Garden. Built in 2019, this property offers a perfect blend of modern finishes, functionality, and prime location. Step inside and enjoy a thoughtfully designed layout featuring upgraded flooring, elegant lighting fixtures, and luxury aluminum handrails that elevate the space. The kitchen stands out as the heart of the home, offering a clean and modern design ideal for both everyday living and entertaining. The primary suite is a true retreat with double walk-in closets and abundant natural light throughout the home, creating a bright and inviting atmosphere. Enjoy added privacy with no rear neighbors and peaceful conservation views—perfect for relaxing after a long day. Location is everything, and this home delivers. Conveniently situated just minutes from top-rated schools, shopping centers, restaurants, golf courses, and major highways, making daily commutes and weekend plans effortless. One of the standout features of this property is the solar panel system, which will be fully paid off at closing—providing significant long-term savings for the new homeowner. This is a rare opportunity to own a move-in ready, upgraded home in a prime Winter Garden location. Schedule your private showing today.

9972 Pallida Hickory Way, Winter Garden
$949,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Experience this beautifully upgraded home built by Toll Brothers, located in the highly desirable Lakeshore community. Perfectly positioned on a premium lot with no front or rear neighbors, this property offers both privacy and stunning surroundings. As you enter the home, you are welcomed by a dramatic two-story foyer highlighted by an elegant wood coffered ceiling, setting the tone for the spacious open concept design. The thoughtfully designed floor plan flows seamlessly into the formal dining area and expansive family room, creating the perfect space for entertaining and everyday living. The gourmet kitchen is a true centerpiece, featuring a large island ideal for gatherings, 42” cabinets with crown molding, stylish tile backsplash, natural gas cooktop, and stainless steel appliances. Just off the kitchen, the family room opens to a covered patio overlooking a private backyard with no rear neighbors, offering a relaxing outdoor retreat with hook ups for outdoor kitchen and sink. The primary suite, conveniently located on the first floor, features coffered ceiling, an upgraded spa-inspired en-suite bathroom, and a custom built walk-in closet. Upstairs, you’ll find a spacious loft with open railing overlooking the foyer below, along with three oversized bedrooms, each equipped with custom walk-in closets, providing comfort and ample storage for everyone. Beyond the home itself, the Lakeshore community offers an exceptional lifestyle with resort style amenities including a fitness center, gathering areas, sand volleyball court, fishing dock, and a spectacular resort style pool with splash area, along with many additional features. Conveniently located near shopping, dining, and top-rated schools, the property also provides easy access to major roadways leading to Walt Disney World Resort, Winter Garden Village, and the vibrant Hamlin area, known for its restaurants, shopping, and movie theater. Schedule your private showing today this exceptional property will not last long.

8216 Topsail Place, Winter Garden
Start Your Search